RU2008148902A - Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) - Google Patents

Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) Download PDF

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Publication number: RU2008148902A
Authority: RU; Russia
Prior art keywords: methyl; alkyl; imidazol; fluoro; amino
Prior art date: 2006-06-27

Application number

RU2008148902/04A

Other languages

English (en)

Russian (ru)

Inventor

Джереми БАРРОУЗ (SE)

Джереми БАРРОУЗ

Фернандо ХУЭРТА (SE)

Фернандо ХУЭРТА

Фредрик ЛАКЕ (SE)

Фредрик ЛАКЕ

Торбен ПЕДЕРСЕН (SE)

Торбен Педерсен

Тобиас РЕЙН (SE)

Тобиас Рейн

Дидье РОТТИЧЧИ (SE)

Дидье Роттиччи

Карин СТААФ (SE)

Карин Стааф

Ульрика ИНГВЕ (SE)

Ульрика ИНГВЕ

Original Assignee

Астразенека Аб (Se)

Астразенека Аб

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2006-06-27

Filing date

2007-06-26

Publication date

2010-08-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=38846127&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=RU2008148902(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2007-06-26 Application filed by Астразенека Аб (Se), Астразенека Аб filed Critical Астразенека Аб (Se)

2010-08-10 Publication of RU2008148902A publication Critical patent/RU2008148902A/ru

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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims 4
201000010099 disease Diseases 0.000 title claims 3
102000001267 GSK3 Human genes 0.000 title 2
108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title 2
KNDAOVHRTCJABP-UHFFFAOYSA-N 1h-imidazole;pyrimidine Chemical class C1=CNC=N1.C1=CN=CN=C1 KNDAOVHRTCJABP-UHFFFAOYSA-N 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract 55
229910052757 nitrogen Inorganic materials 0.000 claims abstract 36
-1 3-tetrahydropyranyl Chemical group 0.000 claims abstract 29
150000001875 compounds Chemical class 0.000 claims abstract 26
125000005843 halogen group Chemical group 0.000 claims abstract 26
229910052799 carbon Inorganic materials 0.000 claims abstract 25
125000000623 heterocyclic group Chemical group 0.000 claims abstract 23
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 20
229910052736 halogen Inorganic materials 0.000 claims abstract 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
239000001257 hydrogen Substances 0.000 claims abstract 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 15
150000002829 nitrogen Chemical class 0.000 claims abstract 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 11
125000004452 carbocyclyl group Chemical group 0.000 claims abstract 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 9
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 7
125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract 6
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 6
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 6
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims abstract 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 5
229910052760 oxygen Inorganic materials 0.000 claims abstract 3
239000001301 oxygen Substances 0.000 claims abstract 3
229920006395 saturated elastomer Polymers 0.000 claims abstract 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
125000004434 sulfur atom Chemical group 0.000 claims abstract 2
125000003545 alkoxy group Chemical group 0.000 claims 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
150000002367 halogens Chemical class 0.000 claims 8
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 7
208000010877 cognitive disease Diseases 0.000 claims 5
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
150000003839 salts Chemical class 0.000 claims 5
206010012289 Dementia Diseases 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 4
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 3
208000028698 Cognitive impairment Diseases 0.000 claims 3
201000011240 Frontotemporal dementia Diseases 0.000 claims 3
208000030886 Traumatic Brain injury Diseases 0.000 claims 3
210000000988 bone and bone Anatomy 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
239000012458 free base Substances 0.000 claims 3
208000024714 major depressive disease Diseases 0.000 claims 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 2
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206010017076 Fracture Diseases 0.000 claims 2
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JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
125000005236 alkanoylamino group Chemical group 0.000 claims 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
230000015572 biosynthetic process Effects 0.000 claims 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
208000027061 mild cognitive impairment Diseases 0.000 claims 2
208000005264 motor neuron disease Diseases 0.000 claims 2
230000002265 prevention Effects 0.000 claims 2
201000000980 schizophrenia Diseases 0.000 claims 2
239000012453 solvate Substances 0.000 claims 2
230000009529 traumatic brain injury Effects 0.000 claims 2
VMGUWFGUMZRWDD-UHFFFAOYSA-N (2,6-dimethylpiperidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CC1CCCC(C)N1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 VMGUWFGUMZRWDD-UHFFFAOYSA-N 0.000 claims 1
WWGYXDWUEUVJCI-UHFFFAOYSA-N (3,3-difluoropyrrolidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCC(F)(F)C1 WWGYXDWUEUVJCI-UHFFFAOYSA-N 0.000 claims 1
HKDAFXBCUWUUQP-UHFFFAOYSA-N (3,5-dimethylpiperidin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1C(C)CC(C)CN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 HKDAFXBCUWUUQP-UHFFFAOYSA-N 0.000 claims 1
PIABFBSAORAFPU-UHFFFAOYSA-N (4-benzylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N(CC1)CCN1CC1=CC=CC=C1 PIABFBSAORAFPU-UHFFFAOYSA-N 0.000 claims 1
FLFRWPXYPISNIH-UHFFFAOYSA-N (4-butan-2-ylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(C(C)CC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 FLFRWPXYPISNIH-UHFFFAOYSA-N 0.000 claims 1
GMQLLYIFZSEJPL-UHFFFAOYSA-N (4-butylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(CCCC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 GMQLLYIFZSEJPL-UHFFFAOYSA-N 0.000 claims 1
OYCCDNYVHVFKKN-UHFFFAOYSA-N (4-ethylpiperazin-1-yl)-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1CN(CC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 OYCCDNYVHVFKKN-UHFFFAOYSA-N 0.000 claims 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
LQEOPALZMNEMPG-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n,n-di(propan-2-yl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C(C)C)C(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 LQEOPALZMNEMPG-UHFFFAOYSA-N 0.000 claims 1
LRMNPLYTCUDBFE-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n,n-dipropylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(CCC)CCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 LRMNPLYTCUDBFE-UHFFFAOYSA-N 0.000 claims 1
YMKZRCIUZLIOHS-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-methyl-n-(2-methylpropyl)pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C)CC(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 YMKZRCIUZLIOHS-UHFFFAOYSA-N 0.000 claims 1
SKAQUBBZLUGQFR-UHFFFAOYSA-N 5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridine-2-carbaldehyde Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(C=O)N=C1 SKAQUBBZLUGQFR-UHFFFAOYSA-N 0.000 claims 1
AFCZSQCTHGPWSN-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(5-methylsulfonylpyridin-2-yl)pyrimidin-2-amine;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)C=N1 AFCZSQCTHGPWSN-UHFFFAOYSA-N 0.000 claims 1
NBKWSGUZFJHXCL-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(6-methylsulfonylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC1=CC=C(S(C)(=O)=O)N=C1 NBKWSGUZFJHXCL-UHFFFAOYSA-N 0.000 claims 1
QKYAWVXVTSDCIM-UHFFFAOYSA-N 5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]-n-(6-propan-2-ylsulfonylpyridin-3-yl)pyrimidin-2-amine Chemical compound C1=NC(S(=O)(=O)C(C)C)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 QKYAWVXVTSDCIM-UHFFFAOYSA-N 0.000 claims 1
QIZMDSPMHSHDEB-UHFFFAOYSA-N 5-fluoro-n-(2-methoxypyrimidin-5-yl)-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(OC)=NC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 QIZMDSPMHSHDEB-UHFFFAOYSA-N 0.000 claims 1
208000017194 Affective disease Diseases 0.000 claims 1
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208000010392 Bone Fractures Diseases 0.000 claims 1
208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
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102100038076 DNA dC->dU-editing enzyme APOBEC-3G Human genes 0.000 claims 1
206010067889 Dementia with Lewy bodies Diseases 0.000 claims 1
208000032131 Diabetic Neuropathies Diseases 0.000 claims 1
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101000742736 Homo sapiens DNA dC->dU-editing enzyme APOBEC-3G Proteins 0.000 claims 1
208000023105 Huntington disease Diseases 0.000 claims 1
201000002832 Lewy body dementia Diseases 0.000 claims 1
241000124008 Mammalia Species 0.000 claims 1
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
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201000004810 Vascular dementia Diseases 0.000 claims 1
MIIHRHZPVFFLNV-UHFFFAOYSA-N [3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C)=N1 MIIHRHZPVFFLNV-UHFFFAOYSA-N 0.000 claims 1
WXPPJJJNBYDKLN-UHFFFAOYSA-N [3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.CN1C(C)=NC=C1C1=NC(NC=2C=C(Cl)C(C(=O)N3CCCCC3)=NC=2)=NC=C1F WXPPJJJNBYDKLN-UHFFFAOYSA-N 0.000 claims 1
HAFDEHIYHASOTC-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=C1Cl)=CN=C1C(=O)N1CCCCC1 HAFDEHIYHASOTC-UHFFFAOYSA-N 0.000 claims 1
SKYXACSXHYZRJQ-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)=N1 SKYXACSXHYZRJQ-UHFFFAOYSA-N 0.000 claims 1
COYKCXSIKZIBPX-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-(oxan-4-yl)-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.N1=C(C=2N(C(=NC=2)C(F)(F)F)C2CCOCC2)C(F)=CN=C1NC(C=C1Cl)=CN=C1C(=O)N1CCCCC1 COYKCXSIKZIBPX-UHFFFAOYSA-N 0.000 claims 1
IMVUQMPEFGNUQU-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)Cl)=NC=C1NC1=NC=C(F)C(C=2N(C(=NC=2)C(F)(F)F)C)=N1 IMVUQMPEFGNUQU-UHFFFAOYSA-N 0.000 claims 1
VXTHKTIWGOTFAH-UHFFFAOYSA-N [3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=C(Cl)C(C(=O)N4CCCCC4)=NC=3)N=2)F)=C1 VXTHKTIWGOTFAH-UHFFFAOYSA-N 0.000 claims 1
QTBWYPYVFWMGBX-UHFFFAOYSA-N [5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C)=N1 QTBWYPYVFWMGBX-UHFFFAOYSA-N 0.000 claims 1
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AQBKDIKKXJXICU-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methoxypiperidin-1-yl)methanone Chemical compound C1CC(OC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 AQBKDIKKXJXICU-UHFFFAOYSA-N 0.000 claims 1
OASYMNQFJRRPSA-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 OASYMNQFJRRPSA-UHFFFAOYSA-N 0.000 claims 1
LPVSGOGWVBRZQH-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-methylpiperidin-1-yl)methanone Chemical compound C1CC(C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 LPVSGOGWVBRZQH-UHFFFAOYSA-N 0.000 claims 1
BGXZVMCGKJNOLZ-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-propan-2-ylpiperazin-1-yl)methanone Chemical compound C1CN(C(C)C)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 BGXZVMCGKJNOLZ-UHFFFAOYSA-N 0.000 claims 1
UVUACLWYQOMFIS-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-(4-propylpiperazin-1-yl)methanone Chemical compound C1CN(CCC)CCN1C(=O)C(N=C1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 UVUACLWYQOMFIS-UHFFFAOYSA-N 0.000 claims 1
GRUMYYBGXQJLOX-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-[4-(4-fluorophenyl)piperazin-1-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N(CC1)CCN1C1=CC=C(F)C=C1 GRUMYYBGXQJLOX-UHFFFAOYSA-N 0.000 claims 1
DTQCTPFWWBHEQQ-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-[4-(4-fluorophenyl)piperidin-1-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N(CC1)CCC1C1=CC=C(F)C=C1 DTQCTPFWWBHEQQ-UHFFFAOYSA-N 0.000 claims 1
MCSBEOQVHGWTJB-UHFFFAOYSA-N [5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]-piperidin-1-ylmethanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCCCC1 MCSBEOQVHGWTJB-UHFFFAOYSA-N 0.000 claims 1
JUMYRNHMMUIHCS-UHFFFAOYSA-N [6-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-3-yl]-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(C=N1)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 JUMYRNHMMUIHCS-UHFFFAOYSA-N 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
231100000360 alopecia Toxicity 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
DVWZSIRIFYGARA-UHFFFAOYSA-N azetidin-1-yl-[3-chloro-5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CN1C(C)=NC=C1C1=NC(NC=2C=C(Cl)C(C(=O)N3CCC3)=NC=2)=NC=C1F DVWZSIRIFYGARA-UHFFFAOYSA-N 0.000 claims 1
IZZMQZVJRXUABE-UHFFFAOYSA-N azetidin-1-yl-[3-chloro-5-[[5-fluoro-4-[3-methyl-2-(trifluoromethyl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone;hydrochloride Chemical compound Cl.N1=C(C(F)(F)F)N(C)C(C=2C(=CN=C(NC=3C=C(Cl)C(C(=O)N4CCC4)=NC=3)N=2)F)=C1 IZZMQZVJRXUABE-UHFFFAOYSA-N 0.000 claims 1
YUDLMHLYKXMDDX-UHFFFAOYSA-N azetidin-1-yl-[5-[[4-(2,3-dimethylimidazol-4-yl)-5-fluoropyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound CN1C(C)=NC=C1C1=NC(NC=2C=NC(=CC=2)C(=O)N2CCC2)=NC=C1F YUDLMHLYKXMDDX-UHFFFAOYSA-N 0.000 claims 1
LJANEJXMXPUPBQ-UHFFFAOYSA-N azetidin-1-yl-[5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]pyridin-2-yl]methanone Chemical compound C1COCCC1N1C(C)=NC=C1C(C(=CN=1)F)=NC=1NC(C=N1)=CC=C1C(=O)N1CCC1 LJANEJXMXPUPBQ-UHFFFAOYSA-N 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
208000028683 bipolar I disease Diseases 0.000 claims 1
208000025307 bipolar depression Diseases 0.000 claims 1
201000011510 cancer Diseases 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
230000001149 cognitive effect Effects 0.000 claims 1
230000007812 deficiency Effects 0.000 claims 1
208000017004 dementia pugilistica Diseases 0.000 claims 1
208000035475 disorder Diseases 0.000 claims 1
208000024732 dysthymic disease Diseases 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
230000035876 healing Effects 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
238000001727 in vivo Methods 0.000 claims 1
208000027866 inflammatory disease Diseases 0.000 claims 1
229910052500 inorganic mineral Inorganic materials 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
238000012423 maintenance Methods 0.000 claims 1
206010027175 memory impairment Diseases 0.000 claims 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
239000011707 mineral Substances 0.000 claims 1
230000036651 mood Effects 0.000 claims 1
XQSRMCZTBCMDDX-UHFFFAOYSA-N n-(6-ethoxypyridin-3-yl)-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(OCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 XQSRMCZTBCMDDX-UHFFFAOYSA-N 0.000 claims 1
BFFHGFGYQRAFPQ-UHFFFAOYSA-N n-(6-ethylsulfonylpyridin-3-yl)-5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-amine Chemical compound C1=NC(S(=O)(=O)CC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 BFFHGFGYQRAFPQ-UHFFFAOYSA-N 0.000 claims 1
CRWPLLBQGBOONW-UHFFFAOYSA-N n-(cyclopropylmethyl)-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-propylpyridine-2-carboxamide Chemical compound C=1C=C(NC=2N=C(C(F)=CN=2)C=2N(C(C)=NC=2)C2CCOCC2)C=NC=1C(=O)N(CCC)CC1CC1 CRWPLLBQGBOONW-UHFFFAOYSA-N 0.000 claims 1
IMWKNRIKTUODBG-UHFFFAOYSA-N n-butan-2-yl-5-[[5-fluoro-4-[2-methyl-3-(oxan-4-yl)imidazol-4-yl]pyrimidin-2-yl]amino]-n-propylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N(C(C)CC)CCC)=CC=C1NC1=NC=C(F)C(C=2N(C(C)=NC=2)C2CCOCC2)=N1 IMWKNRIKTUODBG-UHFFFAOYSA-N 0.000 claims 1
230000011164 ossification Effects 0.000 claims 1
230000007170 pathology Effects 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
230000000750 progressive effect Effects 0.000 claims 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 claims 1
125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
208000022610 schizoaffective disease Diseases 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
235000014347 soups Nutrition 0.000 claims 1
230000006641 stabilisation Effects 0.000 claims 1
238000011105 stabilization Methods 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
208000018726 traumatic encephalopathy Diseases 0.000 claims 1
208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
0 CCIC(Nc1nc(-c2cnc(C)[n]2*)c(*)cn1)=* Chemical compound CCIC(Nc1nc(-c2cnc(C)[n]2*)c(*)cn1)=* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Psychiatry (AREA)
Diabetes (AREA)
Orthopedic Medicine & Surgery (AREA)
Pain & Pain Management (AREA)
Endocrinology (AREA)
Epidemiology (AREA)
Psychology (AREA)
Emergency Medicine (AREA)
Hematology (AREA)
Obesity (AREA)
Dermatology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyridine Compounds (AREA)

RU2008148902/04A 2006-06-27 2007-06-26 Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3) RU2008148902A (ru)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81675606P	2006-06-27	2006-06-27
US60/816,756		2006-06-27

Publications (1)

Publication Number	Publication Date
RU2008148902A true RU2008148902A (ru)	2010-08-10

Family

ID=38846127

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
RU2008148902/04A RU2008148902A (ru)	2006-06-27	2007-06-26	Производные имидазол-пиримидина для лечения заболеваний, связанных с киназой гликогенсинтазы 3 (gsk3)

Country Status (20)

Country	Link
US (1)	US20080188502A1 (zh)
EP (1)	EP2046782A4 (zh)
JP (1)	JP2009542638A (zh)
KR (1)	KR20090024817A (zh)
CN (1)	CN101511825A (zh)
AR (1)	AR061652A1 (zh)
AU (1)	AU2007265731A1 (zh)
BR (1)	BRPI0713576A2 (zh)
CA (1)	CA2655441A1 (zh)
CL (1)	CL2007001881A1 (zh)
CO (1)	CO6140059A2 (zh)
EC (1)	ECSP088973A (zh)
IL (1)	IL195666A0 (zh)
MX (1)	MX2008015720A (zh)
NO (1)	NO20090327L (zh)
RU (1)	RU2008148902A (zh)
TW (1)	TW200815418A (zh)
UY (1)	UY30440A1 (zh)
WO (1)	WO2008002244A2 (zh)
ZA (1)	ZA200810484B (zh)

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US7745428B2 (en)	2005-09-30	2010-06-29	Astrazeneca Ab	Imidazo[1,2-A]pyridine having anti-cell-proliferation activity
AR058073A1 (es) *	2005-10-03	2008-01-23	Astrazeneca Ab	Derivados de imidazol 5-il-pirimidina, procesos de obtencion, composiciones farmaceuticas y usos
TW200811169A (en) *	2006-05-26	2008-03-01	Astrazeneca Ab	Chemical compounds
PT2248812E (pt) *	2006-06-27	2014-03-12	Takeda Pharmaceutical	Compostos cíclicos fundidos como moduladores do receptor gpr40
TW200815417A (en) *	2006-06-27	2008-04-01	Astrazeneca Ab	New compounds II
EP2025674A1 (de)	2007-08-15	2009-02-18	sanofi-aventis	Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
CA2754685A1 (en)	2009-03-11	2010-09-16	Pfizer Inc.	Substituted indazole amides
MX2011010732A (es)	2009-04-15	2011-11-18	Astrazeneca Ab	Pirimidinas sustituidas por imidazol utiles en el tratamiento de trastornos relacionados con glucogeno sintasa cinasa 3 como la enfermedad de alzheimer.
WO2011107494A1 (de)	2010-03-03	2011-09-09	Sanofi	Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
US8933024B2 (en)	2010-06-18	2015-01-13	Sanofi	Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases
US8530413B2 (en)	2010-06-21	2013-09-10	Sanofi	Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215388A (en)	2010-07-05	2012-04-16	Sanofi Sa	(2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201215387A (en)	2010-07-05	2012-04-16	Sanofi Aventis	Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
TW201221505A (en)	2010-07-05	2012-06-01	Sanofi Sa	Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
WO2013037390A1 (en)	2011-09-12	2013-03-21	Sanofi	6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013045413A1 (en)	2011-09-27	2013-04-04	Sanofi	6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
CN103724207B (zh) *	2013-12-20	2016-07-06	北京智博高科生物技术有限公司	苯基苄基醚类衍生物及其制备方法和应用
US20170209488A1 (en)	2014-07-17	2017-07-27	Inserm (Institut National De La Sante Et De La Recherche Medicale)	Methods for treating neuromuscular junction-related diseases
UY36547A (es)	2015-02-05	2016-06-01	Bayer Cropscience Ag	Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas
WO2016207366A1 (en)	2015-06-26	2016-12-29	INSERM (Institut National de la Santé et de la Recherche Médicale)	Methods and pharmaceutical compositions for the treatment of viral infections
PE20180783A1 (es)	2015-08-07	2018-05-07	Bayer Cropscience Ag	Derivados heterociclicos condensados sustituidos por 2-(het) arilo como pesticidas
GB201519573D0 (en)	2015-11-05	2015-12-23	King S College London	Combination

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GB0021726D0 (en) *	2000-09-05	2000-10-18	Astrazeneca Ab	Chemical compounds
JP4570955B2 (ja) *	2002-07-09	2010-10-27	バーテクスファーマスーティカルズインコーポレイテッド	プロテインキナーゼ阻害活性を持つイミダゾール類
JP2007500178A (ja) *	2003-07-30	2007-01-11	サイクラセル・リミテッド	プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体
CA2542880A1 (en) *	2003-10-21	2005-05-12	Cyclacel Limited	Pyrimidin-4-yl-3, 4-thione compounds and their use in therapy
GB0402653D0 (en) *	2004-02-06	2004-03-10	Cyclacel Ltd	Compounds
BRPI0517426A (pt) *	2004-12-17	2008-10-07	Astrazeneca Ab	composto, processo para preparar o mesmo, composição farmacêutica, uso de um composto, e, métodos para produzir um efeito anti-proliferação celular, para produzir um efeito inibitório de cdk2, e para tratar uma doença em um animal de sangue quente
GB0504753D0 (en) *	2005-03-08	2005-04-13	Astrazeneca Ab	Chemical compounds
AR058073A1 (es) *	2005-10-03	2008-01-23	Astrazeneca Ab	Derivados de imidazol 5-il-pirimidina, procesos de obtencion, composiciones farmaceuticas y usos
TW200815417A (en) *	2006-06-27	2008-04-01	Astrazeneca Ab	New compounds II

2007
- 2007-06-21 TW TW096122338A patent/TW200815418A/zh unknown
- 2007-06-26 RU RU2008148902/04A patent/RU2008148902A/ru not_active Application Discontinuation
- 2007-06-26 KR KR1020097001642A patent/KR20090024817A/ko not_active Withdrawn
- 2007-06-26 WO PCT/SE2007/000620 patent/WO2008002244A2/en not_active Ceased
- 2007-06-26 CL CL200701881A patent/CL2007001881A1/es unknown
- 2007-06-26 BR BRPI0713576-9A patent/BRPI0713576A2/pt not_active IP Right Cessation
- 2007-06-26 JP JP2009518044A patent/JP2009542638A/ja active Pending
- 2007-06-26 CN CNA2007800322107A patent/CN101511825A/zh active Pending
- 2007-06-26 MX MX2008015720A patent/MX2008015720A/es not_active Application Discontinuation
- 2007-06-26 AR ARP070102831A patent/AR061652A1/es not_active Application Discontinuation
- 2007-06-26 AU AU2007265731A patent/AU2007265731A1/en not_active Abandoned
- 2007-06-26 CA CA002655441A patent/CA2655441A1/en not_active Abandoned
- 2007-06-26 UY UY30440A patent/UY30440A1/es unknown
- 2007-06-26 EP EP07748281A patent/EP2046782A4/en not_active Withdrawn
- 2007-06-27 US US11/769,102 patent/US20080188502A1/en not_active Abandoned
2008
- 2008-12-02 IL IL195666A patent/IL195666A0/en unknown
- 2008-12-10 ZA ZA200810484A patent/ZA200810484B/xx unknown
- 2008-12-12 EC EC2008008973A patent/ECSP088973A/es unknown
- 2008-12-17 CO CO08134161A patent/CO6140059A2/es unknown
2009
- 2009-01-21 NO NO20090327A patent/NO20090327L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AR061652A1 (es)	2008-09-10
NO20090327L (no)	2009-02-09
TW200815418A (en)	2008-04-01
ZA200810484B (en)	2009-08-26
KR20090024817A (ko)	2009-03-09
MX2008015720A (es)	2008-12-19
CN101511825A (zh)	2009-08-19
JP2009542638A (ja)	2009-12-03
ECSP088973A (es)	2009-01-30
US20080188502A1 (en)	2008-08-07
EP2046782A4 (en)	2010-10-13
WO2008002244A8 (en)	2008-10-09
UY30440A1 (es)	2008-01-31
CA2655441A1 (en)	2008-01-03
WO2008002244A2 (en)	2008-01-03
WO2008002244A3 (en)	2008-02-14
IL195666A0 (en)	2009-09-01
EP2046782A2 (en)	2009-04-15
BRPI0713576A2 (pt)	2012-10-23
CO6140059A2 (es)	2010-03-19
CL2007001881A1 (es)	2008-02-08
AU2007265731A1 (en)	2008-01-03

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2011-10-27	FA92	Acknowledgement of application withdrawn (lack of supplementary materials submitted)	Effective date: 20110913